
Waterfront holiday rentals in Oldsmar
Find and book unique waterfront accommodation on Airbnb
Top-rated waterfront accommodation in Oldsmar
Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

The Zen Den Studio
Welcome to our home away from home, where you can relax and take it easy or enjoy all the excitement close by. Our Seaside Studio sleeps 2 guests comfortably, one queen size bed, one queen sofa bed, 1 full bath, and a fully stocked kitchen. Our studio provides all the amenities of a home with an extraordinary location close to all of your vacation needs. You can take a walk to the Blue Jays Stadium, you are 1 Mile to Downtown Dunedin where restaurants and shops awaiting to please your palate.

Private 1 Bed Apt with Pool and water front.
Enjoy the use of the onsite pool and Private 1-bedroom apartment in a peaceful waterfront community! Equipped with your own kitchenette and separate living area. Enjoy the serenity of swimming in your own pool on your vacation or relaxing work stay. Lounge chairs will make your stay even more relaxing. Close to the Veterans expressway and easy access to local restaurants, beaches, 10 minutes from the airport, 20 minutes from the river walk, and entertainment. This apartment is 300 square feet

salt living at its best
- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

Lakefront home near beaches w/ waterview, pets ok
Imagine yourself waking up to a million-dollar view on Tampa Bay's largest lake - lake Tarpon. Close your eyes, relax and lose yourself to the sound of wind chimes, the caws and squeals of the birds, lapping of waves against the dock and fresh lake breeze. Watch an Osprey catch fish and other wildlife as you sip your morning coffee sitting on the dock. This is a quintessential lake house that one always desires in their dreams. Well that dream is attainable when you make this home your abode!

Stars by the Sea - Cozy home close to beaches
Our home is beautifully updated, fully furnished and decorated in a beach theme. The master bedroom has a comfortable king size bed and the second bedroom has a queen. We have a beautiful pond in the back. Perfect for you to relax and BBQ while enjoying our wonderful Florida weather. The house has a Smart TV, Internet w/Wi-Fi, dishwasher, washer, dryer, and much more. Everything you need to make your stay perfect. We are close to great shopping, dining and to some of Florida's best beaches.

Bay Lake Cottage
You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake.Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

Tree House Treasure
We're a quiet, small, serene old neighborhood on the end of a cul-de-sac and nearly floating on a lagoon! Florida nature at it's finest. The home is just 4 feet off the sea wall so the home is best suited for adults that are looking for that quiet get-a-way. Upper has 2 beds & a tri-fold mattress. Our driveway is shared so we can accommodate for one vehicle and it must fit under our carport and there is no street parking. No smoking, vaping, or illegal drugs permitted.

Bayside Retreat your tropical oasis
"Bayside Retreat" is a Charming Private 1~bedroom/1 bath with full living room suite, located right on the water of upper Tampa Bay. Spend a quiet day lounging in the grotto pool, kayaking the bay, or a lazy day reading in the hammock. Enjoy breath taking sunrise and sunsets from the dock. Your own Tropical Paradise away from the rest of the world....... Just 15min to Raymond James Stadium. Centrally located 15 miles from TPA Airport

Tranquil poolside guesthouse on the river
The apartment is on the Hillsborough River surrounded by nature but only 3 minutes away from the great restaurants, bars and breweries of Seminole Heights. It is walking distance to Lowry Park Zoo and park. Spot the beautiful Florida wildlife up close from the river dock. Soak in the outdoor pool surrounded by mature live oaks or take a canoe out on the river. Top beaches are 35 minutes by car. Great for a couple or a small family.

Tarpon Lake Escape LLC
Key West-inspired, newly furnished house on Lake Tarpon. Decorated in bright Key West style! 3 bedrooms, 2 bathrooms, 2 porches, and a ping pong table on a corner lot with over 190 feet of water property. One of the best properties on the lake! Innisbrook Golf Resort is 1/2 mile away Clearwater Beach 15 mi Tarpon Springs Sponge Docks 5 mi Downtown Dunedin 9.6mi Honeymoon Island 8.7mi TPA airport 20mi Raymond James Stadium 20mi

Kayaks & Firepit Mins to Dwntwn!
River Front One Bedroom Apartment in Trendy Seminole Heights, the best Restaurant District In Tampa -Fast Wifi and Smart TV -Includes Use of Kayaks and Canoes -Wood Burning Fire Pit -15 Minutes from Cypress Point Park Beach and the Airport and YBOR City, the Mid Florida Ampitheatre, and the Seminole Casino -10 Minutes from Downtown, the Convention Center, RiverWalk and Armature Works, and Julian Lane Park

Spacious Lakehouse Suite - Nature Lover's Paradise
Bright, clean & well appointed Private patio entrance Includes bedroom, private bathroom & sitting room with TV, microwave, etc. PLEASE TAKE NOTE: the suite shares walls & closed/locked doors with host's home. Spacious lakeside deck & canoe FOR A PRIVATE/ROMANTIC GETAWAY consider our other listing on the property - Miss Ruby, our fully renovated vintage camper with open-air shower and bath-house.
Popular amenities for Oldsmar waterfront rentals
Waterfront apartment accommodation

The Palm Bayview Balcony, Bar & Grill, Heated Pool

Anchors UP #2, WALK to Beach, 1 bed/1 bath apt.

Elegant Waterfront Condo with Pool Private Balcony

Beachy Bayfront Condo Walk to Beach

Ocean Front Condo!

Direct Ocean View Top Floor Renovated. 2BR, 2 Bath

Gorgeous and Updated Waterfront Condo 2 Bed/2 Bath

The Oasis
Waterfront house rentals

Gulf Harbors Getaway Home with Pool

Ocean Sunsets & Downtown Biking Trails

Casa Del Sole

Waterfront Resort with HEATED POOL!

Beautiful two bedroom w/ pool table & free parking

3BR Waterfront House I Raymond James Stadium

Boaters Paradise- Waterfront Heated Pool King Beds

NEW Heated Salt Pool & Spa on Waterfront Canal
Waterfront condo accommodation

Tampa Events & Suite w/WtrFrt Bay & Sunset Views

Tampa Bay Near by Airport & Stadium

Sea La Vie- Studio by the bay!

Rocky Point paradise

Tropical Beachfront Penthouse-Beach Cottages

Walk Everywhere! Beach, Pier 60, Dining, Nightlife

Waterfront condo on top floor @ Boca Ciega Resort

Charming Condo next to Honeymoon Island
Quick stats about waterfront rentals in Oldsmar

Total holiday rentals
Explore 10 holiday rentals in Oldsmar

Nightly prices starting at
Oldsmar holiday rentals start at $53 NZD per night before taxes and fees

Verified guest reviews
Over 1,160 verified reviews to help you choose

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
10 of Oldsmar holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Oldsmar rentals

4.9 Average rating
Oldsmar stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- Saint Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Fitness-friendly rentals Oldsmar
- House rentals Oldsmar
- Rentals with a fireplace Oldsmar
- Hotel rentals Oldsmar
- Rentals with pools Oldsmar
- Rentals with a fire pit Oldsmar
- Rentals with a patio Oldsmar
- Rentals with beach access Oldsmar
- Pet-friendly rentals Oldsmar
- Rentals with a washing machine and dryer Oldsmar
- Rentals with outdoor seating Oldsmar
- Family-friendly rentals Oldsmar
- Waterfront rentals Pinellas County
- Waterfront rentals Florida
- Waterfront rentals United States
- Anna Maria Island
- John's Pass
- Raymond James Stadium
- Weeki Wachee Springs
- Busch Gardens Tampa Bay
- Dunedin Beach
- Coquina Beach
- Cortez Beach
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- River Strand Golf and Country Club
- Adventure Island
- Tampa Palms Golf & Country Club
- Splash Harbour Water Park
- Honeymoon Island Beach
- North Beach At Fort DeSoto Park
- Busch Gardens
- Fred Howard Park